Piperidine → 5-Acetonyl-3-piperidinomethyl-1,2,4-oxadiazole

HRID 247110Notes

Reaction equation

HRID 247110 reaction equation
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10]Cl)[N:6]=1)[C:2]([CH3:4])=[O:3].C(N(CC)CC)C.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1>[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:6]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazole

Product 1

HCID 138247065-Acetonyl-3-piperidinomethyl-1,2,4-oxadiazoleYield 56.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15.0 g of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole in 50 ml of THF were added dropwise 17.4 g of triethylamine and subsequently 11.0 g of piperidine. The mixture was stirred at room temperature for 24 hours and then heated under reflux for 6 hours. After cooling, the precipitated material was removed by filtration and the filtrate was evaporated in vacuo. The residue was chromatographed on silica gel using chloroform-methanol (20:1, v/v) as eluent to give 10.9 g of 5-acetonyl-3-piperidinomethyl-1,2,4-oxadiazole as a colorless solid, m.p. 66°-67° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. customthe precipitated material was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-424a10afc27f4ca58e6791c1a2642d37
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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